Guest-templated selection and amplification of a receptor by noncovalent combinatorial synthesis

Angewandte Chemie - International Edition

Volumn 39, Issue 4, 2000, Pages 755-758

  Calama, Mercedes Crego ^a   Timmerman, Peter ^a   Reinhoudt, David N ^a  

^a UNIVERSITY OF TWENTE   (Netherlands)

Author keywords

Combinatorial chemistry; Host guest chemistry; Hydrogen bonds; Noncovalent interactions; Supramolecular chemistry

Indexed keywords

BARBITAL; MELAMINE; PORPHYRIN DERIVATIVE; PYRIDINE DERIVATIVE; RECEPTOR;

ARTICLE; CHEMICAL REACTION; DIRECTED MOLECULAR EVOLUTION; HYDROGEN BOND; MOLECULAR RECOGNITION; RECEPTOR AFFINITY; STOICHIOMETRY; SYNTHESIS; THERMODYNAMICS;

EID: 0034681496     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000218)39:4<755::AID-ANIE755>3.0.CO;2-6     Document Type: Article

References (48)

1. a) S. Anderson, H. L. Anderson, J. K. M. Sanders, Acc. Chem. Res. 1993, 26, 469-475, and references therein;
2. b) R. Hoss, F. Vögtle, Angew. Chem. 1994, 106, 389-398;
3. Angew. Chem. Int. Ed. Engl. 1994, 33, 375-384, and references therein;
4. c) D. M. Rudkevich, J. Rebek, Jr., Angew. Chem. 1997, 109, 877-879;
5. Angew. Chem. Int. Ed. Engl. 1997, 36, 846-848;
6. d) R. G. Chapman, N. Chopra, E. D. Cochien, J. C. Sherman, Tetrahedron 1997, 53, 15911-15946;
7. e) A. M. A. van Wageningen, P. Timmerman, J. P. M. van Duynhoven, W. Verboom, F. C. J. M. van Veggel, D. N. Reinhoudt, Chem. Eur. J. 1997, 3, 639-654.
8. For some examples, see: a) R. G. Chapman, J. C. Sherman, J. Am. Chem. Soc. 1995, 117, 9081-9082;
9. b) B. Hasenkopf, J.-M. Lehn, N. Boumediene, A. Dupont-Gervais, A. van Dorsselaer, B. Kneisel, D. Fenske, J. Am. Chem. Soc. 1997, 119, 10956-10962;
10. c) M. C. T. Fyfe, P. T. Glink, S. Menzer, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 1997, 109, 2158-2160;
11. Angew. Chem. Int. Ed. Engl. 1997, 36, 2068-2070;
12. d) F. Ibukuro, T. Kusukawa, M. Fujita. J. Am. Chem. Soc. 1998, 120, 8561 -8562.
13. G. Wulff, Angew. Chem. 1995, 107, 1958-1979;
14. Angew. Chem. Int. Ed. Engl. 1995, 34, 1812-1832, and references therein.
15. a) A. V. Eliseev, M. I. Nelen, J. Am. Chem. Soc. 1997, 119, 1147-1148;
16. b) A. V. Eliseev, M. I. Nelen, Chem. Eur. J. 1998, 4, 825-834.
17. a) P. A. Brady, J. K. M. Sanders, J. Chem. Soc. Perkin Trans. 1 1997, 3237-3253;
18. b) H. Hioki, W. C. Still, J. Org. Chem. 1998, 63, 904-905;
19. c) M. Albrecht, O. Bau, R. Fröhlich, Chem. Eur. J. 1999, 5, 48-56;
20. d) I. Hue, M. J. Krische, D. P. Funeriu, J.-M. Lehn, Eur. J. Inorg. Chem. 1999, 1415-1420.
21. For recent overviews, see: a) A. Ganesan, Angew. Chem. 1998, 110, 2989-2992;
22. Angew. Chem. Int. Ed. 1998, 37, 2828-2831, and references therein;
23. b) C. Gennari, H. P. Nestler, U. Piarulli, B. Salom, Liebigs Ann. 1997, 637-647, and references therein;
24. J.-M. Lehn, Chem. Eur. J. 1999, 5, 2455-2463.
25. Several examples of host-templated selection of the strongest binder in a dynamic library of guest molecules were recently reported: a) I. Hue, J.-M. Lehn, Proc. Natl. Acad. Sci. USA 1997, 94, 2106-2110;
26. b) S. Sakai, Y. Shigemassa, T. Sasaki, Tetrahedron Lett. 1997, 38, 8145-8148;
27. c) B. Klekota, M. H. Hammond, B. L. Miller, Tetrahedron Lett. 1997, 38, 8639-8642.
28. a) S. J. Rowan, P. A. Brady, J. K. M. Sanders, Angew. Chem. 1996, 108, 2283-2285;
29. Angew. Chem. Int. Ed. Engl. 1996, 35, 2143-2145;
30. b) S. J. Rowan, J. K. M. Sanders, Chem. Commun. 1997, 1407-1408;
31. c) S. J. Rowan, P. A. Brady, J. K. M. Sanders, J. Am. Chem. Soc. 1997, 119, 2578-2579.
32. a) R. H. Vreekamp, J. P. M. van Duynhoven, M. Hubert, W. Verboom, D. N. Reinhoudt, Angew. Chem. 1996, 108, 1306-1309;
33. Angew. Chem. Int. Ed. Engl. 1996, 35, 1215-1218;
34. b) P. Timmerman, R. H. Vreekamp, R. Hulst, W. Verboom, D. N. Reinhoudt, K. Rissanen, K. A. Udachin, J. Ripmeester, Chem. Eur. J. 1997, 3, 1823-1832;
35. K. A. Jolliffe, M. Crego Calama, P. Timmerman, R. Fokkens, N. M. M. Nibbering, D. N. Reinhoudt, Angew. Chem. 1998, 110, 1294-1297;
36. Angew. Chem. Int. Ed. 1998, 57, 1247-1251;
37. d) L. J. Prins, J. Huskens, F. de Jong, P. Timmerman, D. N. Reinhoudt, Nature 1999, 398, 498-502.
38. For a general overview of noncovalent synthesis, see: G. M. Whitesides, E. E. Simanek, J. P. Mathias, C. T. Seto, D. N. Chin, M. Mammen, D. M. Gordon, Acc. Chem. Res. 1995, 25, 37-44, and references therein.
39. M. Crego Calama, R. Hulst, R. Fokkens, N. M. M. Nibbering, P. Timmerman, D. N. Reinhoudt, Chem. Commun. 1998, 1021-1022.
40. 2+1/6N(N-1)(N-2).
41. Dimelamine 2 was synthesized in 60% yield (two steps) by the reaction of the bis(chlorotriazine) derivative 3 with (excess) 1,3-propane diamine followed by reaction with Zn-[5-(4-chlorocarbonylphenyl)-10,15,20-tris(4-methylphenyl)-porphyrin] (1.2 equiv).
42. H. L. Anderson, J. K. M. Sanders, J. Chem. Soc. Chem. Commun. 1989, 1714-1715.
43. H. L. Anderson, J. K. M. Sanders, Angew. Chem. 1990, 102, 1478-1480;
44. Angew. Chem. Int. Ed. Engl. 1990, 29, 1400-1403.
45. 1H NMR spectrum of the library is not very informative due to extensive overlap of signals for homomeric and heteromeric assemblies.
46. f, g). The calculated distribution of 25/75 % reflects the threefold higher probability for formation of the heteromeric assemblies.
47. 2. Evidence for this comes from the fact that the intensity of these signals increases when 4 is present in larger excess.
48. P. Timmerman, D. N. Reinhoudt, Adv. Mater. 1999, 11, 71-74.